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Dating While Dieting Pt. 1: A Cautionary Don't Do It (Yet) Tale


I met my first boyfriend 40 pounds into my third weight loss journey at the age of 23. It took me all of two weeks into us talking for me to start skipping workouts to be home just in case he wanted to come over because I was that damn thirsty for a boyfriend and he was that damn non-committal. Of course it didn't take long before the pounds lost returned and then some, as I turned to everything but my own self-worth to cope with a tumultuous three-year-off-and-on relationship that, in a word, could best be summed up as disrespectful. But nobody else was trying to make me their girlfriend, a fact I chalked up to my weight, and since he kept coming back to me too I figured that meant my size wasn't a problem for him. That is until we were riding the bus together under peculiar circumstances and the man who'd once written "It didn't bother me that Brandy was a heavy set girl, because she was pretty as hell," told me he wanted me to lose weight because he was concerned about my health.

I won't explain said peculiar circumstances right now because I can only take so much judgement in one day, but let's just say I felt he was in no position to ask anything of me. And considering the number he did on my mental health during our relationship, I found his "concern" as laughable as the fact that he couldn't even spell my damn name right. I also told myself what he was really concerned about was being seen with me, which would explain the plethora of in-house "dates" we had while together. And so I copped the tude of attitudes with him, not because I was angry, but because I was hurt.

Being overweight is like the personification of a yo mama joke, nobody else can talk about it but you, and you especially don't want the person whose approval you seek most calling out something in your mind you think they don't see. Note: this is before I understood the concept of loving someone because of, not in spite of so-called flaws. Nevertheless, I was mortified at his suggestion of weight loss and my mind ran with my then-boyfriend's words, confirming narratives I'd already had in my mind, like "all men see when they look at me is my weight" and "If only I was thinner some knucklehead would love me." As it turns out, simply being thinner isn't a remedy for all that negative programming over the years.

During my last weight loss journey, I wasn't really pressed to date because in my mind my smaller milkshake was destined to bring all the boys to the yard, it was just a matter of time. But when people kept asking me how my dating life had changed the smaller I got and I realized it really hadn't. I started questioning whether I'd gotten the school bell time wrong or maybe I'd just been duped.

"Are you approaching men the same way you did when you were bigger?" one of my friends would ask every time I sent her one of my "I'm lonely AF" texts. I never quite understood what she meant by that. I didn't approach men when I was overweight and I wasn't approaching them now... ohhhhh maybe that's what was supposed to change. Well, in a way it kind of did. I decided to hop on a dating app or two and test my "If I was thinner" theory, but dating while smaller only opened up a new set of concerns.

When setting up my profile I was very conscious of making sure I had at least two or three full body shots because I wanted whoever was about to swipe on me to know what they were getting into, i.e. I was still behaving as though my physical size was the most important factor in my dateability and as though my dating pond was still limited to chubby chasers (a fact that wasn't even true at my heaviest). But then I would cringe at the thought of a potential date googling me and seeing all the before and after photos from my articles on my weight loss journey. What would they think of me, knowing that I used to be so big? Will they be afraid that I'll just gain it all back? Do I tell them I've lost x amount of pounds and I'm still trying to lose more? Do I have to explain why I'm eating a salad? Do I have the willpower to only eat a salad and honor my commitment to myself? Overall, I was proud of my success but fearful of sharing too much too soon with men who wouldn't understand my journey.

Though somewhere in my mind giving in to that concern felt disingenuous to myself, the fear was realized when I briefly dated a guy who actually knew me at my heaviest. Early last year, I was in the midst of a half-assed attempt to get back on track after regaining 20 pounds or so and I'd gotten back in contact with a guy I knew through a mutual friend. He was a gym rat who ate grilled chicken and vegetables for lunch every day without ceasing so, naturally, I thought this pairing could only lead to good things. But when a story on the train ride back uptown about his dialysis patients dying on him turned into "that's why I want you to get serious about your weight loss again so you don't get diabetes like your mom and end up like my patients" I was stunned; literally breathless.

First of all, what is it with New York men and health heart-to-hearts on public transportation? And second, no, just no. Because I was still that same insecure 23-year-old, I did what I know how to do: get angry. I told him he didn't know me well enough to give a fuck if I died or not and I shut down for the rest of the night. I knew, again, I'd heard what I wanted to hear -- that he wasn't attracted to me, that all he saw was my weight -- but I was hurt. I thought if anyone would understand my journey it would be someone who'd already seen me make the necessary changes to drop several pounds. But he just didn't get it, and I was clearly still too ashamed, emotional and sensitive about my weight at every size to explain it to anyone -- not exactly grounds for good relationship communication.

I realized the same hangups I had while plus-size didn't miraculously go away because I'd become the size of the average American woman (must be what my friend was implying). There was still a great deal of shame and assuming (one of my favorite activities) on my part about the way men experience me. And it wasn't until I got some necessary feedback from other previous men in my life who told me my weight was never an issue for them but pointed out some other things that were, like putting up walls and refusing to let them get close, that I realized I was responsible for my relationship issues. Not my weight, which was just an outward reflection of my internal mess, but me as a person, the person who was still using the weight I no longer physically had as an emotional barrier to getting close to someone. The obvious conclusion there was until I tackled that issue I didn't have any business dating anybody; and that pretty much still rings true today, though I have made some positive changes. Stay tuned for part 2.

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